Woolford Vacation Packages
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Your Woolford Vacation
Say bye-bye to the stress of planning and hello to a Woolford vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Downtown Cambridge, which is good for bars and pubs, culture and cafes. In the mood for a bit of sightseeing? A trip to Woolford wouldn't be complete without checking out Harriet Tubman Underground Railroad National Historical Park, Spocott Windmill and other major attractions. Your ideal Woolford vacation is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored just for you.
Top Woolford Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront
Downtown Ocean City
Price was CA $684, price is now CA $641 per person
CA $641
per person
Mar 21 - Mar 23
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9/10 Wonderful! (3,316 reviews)
The only place we stay when we go to Ocean City. Great location, plenty of parking, friendly staff, good food, 2 arcade areas! On the boardwalk, far enough from the inlet crowds, but a nice walk. Great beach location & views.
Reviewed on Feb 1, 2026
Woolford Hotel Deals
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford MD
9.8/10 Exceptional! (58 reviews)
The home is in a stunning location, and was perfect for our family gathering over the Thanksgiving holiday. Everything you need for a relaxing, enjoyable getaway is provided in this home, and we’d absolutely stay there again!
Reviewed on Dec 1, 2025
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford MD
9.4/10 Exceptional! (25 reviews)
Comfortable house near Cambridge for a three day stay. Would stay again!
Reviewed on Dec 14, 2025
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Feb 12 to Feb 13
CA $254
CA $328 total
Feb 12 - Feb 13
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Nice stay, but a little too crowded.
Reviewed on Jan 30, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
